Abstract
Structural analysis of two new β-lactam antibiotics, A16884A and A16886B, indicated that they, like cephalosporin C, were composed of modified valine and cysteine residues, and α-aminoadipic acid. However, acid hydrolysis of A16886B and A16884A produced three times as much glycine as did hydrolysis of cephalosporin C under the same conditions. Samples of A16886B-14C-6 and A16886B-14C-8 were prepared by the addition of cysteine-14C-3 and cystine-14C-1 to fermentations of Streptomyces clavuligerus. The specific activity of glycine obtained from hydrolysis of A16886B-14C-6 was considerably higher than that from hydrolysis of A16886B-14C-8. An explanation for the difference in amounts of glycine obtained from hydrolysis of these antibiotics is discussed.
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- ABRAHAM E. P., NEWTON G. G. Synthesis of D-delta-amino-delta-carboxyvalerylglycine (a degradation product of cephalosporin N) and of DL-delta-amino-delta-carboxyvaleramide. Biochem J. 1954 Oct;58(2):266–268. doi: 10.1042/bj0580266. [DOI] [PMC free article] [PubMed] [Google Scholar]
- ARNSTEIN H. R., GRANT P. T. The biosynthesis of penicillin. 2. The incorporation of cystine into penicillin. Biochem J. 1954 Jul;57(3):360–368. doi: 10.1042/bj0570360. [DOI] [PMC free article] [PubMed] [Google Scholar]
- CHAPPELLE E. W., LUCK J. M. The decarboxylation of amino acids, proteins, and peptides by N-bromosucclnimide. J Biol Chem. 1957 Nov;229(1):171–179. [PubMed] [Google Scholar]
- JEFFERY J. D., ABRAHAM E. P., NEWTON G. G. Further degradation products of cephalosporin C. Isolation and synthesis of 2-(4-amino-4-carboxybutyl)thiazole-4-carboxylic acid. Biochem J. 1960 May;75:216–223. doi: 10.1042/bj0750216. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Nagarajan R., Boeck L. D., Gorman M., Hamill R. L., Higgens C. E., Hoehn M. M., Stark W. M., Whitney J. G. Beta-lactam antibiotics from Streptomyces. J Am Chem Soc. 1971 May 5;93(9):2308–2310. doi: 10.1021/ja00738a035. [DOI] [PubMed] [Google Scholar]
- Whitney J. G., Brannon D. R., Mabe J. A., Wicker K. J. Incorporation of labeled precursors into A16886B, a novel -lactam antibiotic produced by Streptomyces clavuligerus. Antimicrob Agents Chemother. 1972 Mar;1(3):247–251. doi: 10.1128/aac.1.3.247. [DOI] [PMC free article] [PubMed] [Google Scholar]